Glycerol → HCID 22000906, compound

HRID 1976305Notes

Reaction equation

HRID 1976305 reaction equation
B(O)(O)O.[CH3:5][C:6]1[CH:7]=[C:8]([OH:16])[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1.C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O.[OH:32][CH2:33]C(CO)O>>[OH:16][C:8]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=[C:6]([CH3:5])[C:7]=1[CH:33]=[O:32]

Participants

6

Reactant 5

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 7628Boric AcidHCID 22000899HCID 22000899, compound

Product 1

HCID 22000906HCID 22000906, compound

Conditions

Temperature
170 °C

Procedure

A suspension of boric acid (5.88 g) in glycerol (20 ml) was heated at 170° C. for 30 minutes. Temperature of the reaction mixture was lowered at 155° C. and 5,6,7,8-tetrahydro-3-methyl-1-naphthol (5.00 g) was added dropwise over 10 minutes. After 15 minutes, hexamethylenetetramine (4.35 g) was added dropwise below 180° C. and stirred at 170° C. for 30 minutes. The mixture was cooled to 110° C. and 24% aqueous sulfuric acid (20 ml) was added. The mixture was steam distilled and AcOEt was added to the distillate. The organic phase was washed with brine and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to give 5,6,7,8-tetrahydro-1-hydroxy-3-methylnaphthalene-2-carbaldehyde as a solid (2.15 g). A pure sample was obtained by recrystallization from EtOH-H2O.

Workup

  1. customwas lowered at 155° C.
  2. temperatureThe mixture was cooled to 110° C.
  3. distillationdistilled
  4. additionAcOEt was added to the distillate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5380031ff8e74f5f84ad1633d36ac5f4
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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