Sulfuric Acid → 4-(Oxan-4-yl)phenol

HRID 1678970Notes

Reaction equation

HRID 1678970 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.S(=O)(=O)(O)[OH:19]>O>[OH:19][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 203654724-(Oxan-4-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 227373584-(Oxan-4-yl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 5.2 g of sodium nitrite in 10 ml of water was added to a mixture of 13 g of 4-(p-aminophenyl)-tetrahydropyran and 100 ml of concentrated sulfuric acid cooled to 5° C and the mixture was stirred at 5° C for 30 minutes. The mixture was poured into a solution of 100 ml of water and 10 ml of concentrated sulfuric acid heated to 75°-80° C and the mixture was held at 75°-80° C for 15 minutes and was then cooled to 4° C. The mixture was filtered and the recovered crystals were washed with water and dried to obtain 12.7 g of 4-(p-hydroxyphenyl)-tetrahydropyran melting at 164° C.

Workup

  1. temperatureheated to 75°-80° C
  2. waitthe mixture was held at 75°-80° C for 15 minutes
  3. temperaturewas then cooled to 4° C
  4. filtrationThe mixture was filtered
  5. washthe recovered crystals were washed with water
  6. customdried

Sources & evidence

ORD record
ord-bafb14dcdae342e7978d6f94a934a8ac
Source dataset
uspto-grants-1978_03
Patent number
US04078076

Reaction notes

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