Hydrochloric Acid → 4-(3-Chloropropyl)phenol

HRID 133773Notes

Reaction equation

HRID 133773 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.[ClH:12]>O>[Cl:12][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 139290484-(3-Chloropropyl)phenolYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(4-Hydroxyphenyl)-1-propanol (0.97 g, 0.006374 mol) and concentrated HCl (20 ml) were heated at 100° C. for 14 h. After being cooled, the reaction mixture was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated in vacuo to give a raw product. Purification by flash chromatography (heptane/ethyl acetate 9:1) gave a pure product (0.98 g, 90%).

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a raw product
  7. customPurification by flash chromatography (heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-5ddef234d35e48a58ec24166d96c46f4
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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