Benzyl Alcohol → Benzyl 6-hydroxyhexanoate

HRID 1197229Notes

Reaction equation

HRID 1197229 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 10401epsilon-CAPROLACTONEHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15224618Benzyl 6-hydroxyhexanoate

Conditions

Temperature
100 °C

Procedure

A mixture of ε-caprolactone (a) (40 g), benzyl alcohol and p-toluenesulfonic acid monohydrate (0.7 g) was stirred at 100° C. for 16 hours. The reaction mixture was treated in the conventional manner and was distilled under reduced pressure (1 mmHg, 140°-154° C.) to give the title compound (b). Yield: 27.37 g (35%)

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. distillationwas distilled under reduced pressure (1 mmHg, 140°-154° C.)

Sources & evidence

ORD record
ord-a96eff94ed2642b5bb4688a786314e94
Source dataset
uspto-grants-1992_05
Patent number
US05117042

Reaction notes

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